5459-93-8

Basic information

• Product Name: N-Ethylcyclohexylamine
• Synonyms: (ethylamino)-cyclohexan;(ethylamino)cyclohexane;Accelerator HX;acceleratorhx;Cyclohexylamine, N-ethyl-;Ethylcyclohexylamine;ethyl-n-cyclohexylamine;N-Cyclohexyl-N-ethylamine
• CAS NO: 5459-93-8
• Molecular Formula: C₈H₁₇N
• Molecular Weight: 127.23
• EINECS: 226-733-8
• Mol File: 5459-93-8.mol
• Article Data: 33

Chemical Properties

• Melting Point: -15°C (estimate)
• Boiling Point: 165 °C(lit.)
• Flash Point: 111 °F
• Appearance: Clear colorless to light yellow/Liquid
• Density: 0.844 g/mL at 25 °C(lit.)
• Vapor Density: 4.4 (vs air)
• Vapor Pressure: 2 mm Hg ( 20 °C)
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 11.16±0.20(Predicted)
• Explosive Limit: 7.6%
• BRN: 2070280
• CAS DataBase Reference: N-Ethylcyclohexylamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Ethylcyclohexylamine(5459-93-8)
• EPA Substance Registry System: N-Ethylcyclohexylamine(5459-93-8)

Safety Data

• Hazard Codes: C
• Statements: 10-20/21/22-35
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 2734 8/PG 2
• WGK Germany: 3
• RTECS: GX1225000
• TSCA: Yes
• HazardClass: 8
• PackingGroup: II
• Hazardous Substances Data: 5459-93-8(Hazardous Substances Data)

Usage

Uses

Used in Herbicide Production:
N-Ethylcyclohexylamine is used as an intermediate in the production of herbicides. It is used for its ability to react with other chemicals to form active ingredients in herbicides, which are used to control, kill, or inhibit the growth of unwanted plants.
Used in Pharmaceutical Production:
N-Ethylcyclohexylamine is also used as an intermediate in the production of pharmaceuticals. It is used for its ability to react with other chemicals to form active pharmaceutical ingredients, which are used to treat various medical conditions.
Used in Synthesis of Isatin-Mannich Bases:
N-Ethylcyclohexylamine can be used in the synthesis of a series of isatin-Mannich bases. These compounds have potential applications in the development of new drugs and pharmaceuticals, as well as in the synthesis of other organic compounds.

Synthesis Reference(s)

Tetrahedron Letters, 37, p. 6749, 1996 DOI: 10.1016/S0040-4039(96)01458-X

Air & Water Reactions

Highly flammable. Slightly soluble in water.

Reactivity Profile

N-Ethylcyclohexylamine neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Flammable gaseous hydrogen may be generated in combination with strong reducing agents, such as hydrides.

Hazard

Corrosive and toxic.

Health Hazard

Inhalation of high concentration of vapor will produce irritation of the respiratory tract and lungs. Inhalation of large quantities of vapor may be fatal.

Fire Hazard

Behavior in Fire: Dangerous when exposed to heat or flame. Can react vigorously with oxidizing materials.

Safety Profile

Moderately toxic by ingestion, inhalation, and skin contact. A severe skin and eye irritant. A very dangerous fire hazard when exposed to heat or flame; can react vigorously with oxidizing materials. To fight fKe, use alcohol foam, mist, spray, dry chemical. See also AMINES

InChI:InChI=1/C22H27FN2/c23-20-8-12-22(13-9-20)25-16-14-24(15-17-25)21-10-6-19(7-11-21)18-4-2-1-3-5-18/h1-5,8-9,12-13,19,21H,6-7,10-11,14-17H2

Upstream product

• 1124-53-4 N-cyclohexylacetamide 
• 627-45-2 N-formylethylamine 
• 108-94-1 cyclohexanone 
• 75-04-7 ethylamine 
• 108-91-8 cyclohexylamine 
• 75-03-6 ethyl iodide 
• 74-96-4 ethyl bromide 
• 32405-88-2 diethyl cyclohexylphosphoramidate 
• 5577-68-4 cyclohexylamino-trimethyl-silane 
• 103-84-4 Acetanilid 
• 64-17-5 ethanol 
• 75-05-8 acetonitrile 
• 108-93-0 cyclohexanol 
• 62-53-3 aniline 

Downstream Products

• 57880-93-0 N-methyl-N-ethyl-cyclohexylamine 
• 564-74-9 N-ethyl-N-cyclohexyl-N',N'-dimethyl-diamidophosphoryl fluoride 
• 69103-74-8 ethyl-cyclohexyl-amidosulfuric acid 
• 2567-61-5 N-cyclohexyl-N-ethylchloroacetamide 
• 14256-70-3 N-ethyl-N-cyclohexyl-ethylenediamine 
• 55412-25-4 2-acetamino-N-ethyl-5-carbethoxy-N-cyclohexyl-benzylamine 
• 13167-44-7 ethylcyclohexylammonium ethylcyclohexyldithiocarbamate 
• 101-81-5 Diphenylmethane 
• 110426-39-6 C₈H₁₆N^(1-)*Li⁽¹⁺⁾ 
• 126989-73-9 4-Chloro-5-(cyclohexyl-ethyl-amino)-2,2-bis-methylsulfanyl-cyclopent-4-ene-1,3-dione 
• 110426-44-3 C₈H₁₆N^(1-)*K⁽¹⁺⁾ 
• 108-88-3 toluene 
• 118060-66-5 5-(N-cyclohexyl-N-ethyl)-aminomethylene-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 80463-72-5 N-cyclohexyl-N-ethyl-4-<(1-methyl-5-tetrazolyl)thio>butyramide 

Relevant articles and documents

A Lewis Base Nucleofugality Parameter, NFB, and Its Application in an Analysis of MIDA-Boronate Hydrolysis Kinetics

The kinetics of quinuclidine displacement of BH3 from a wide range of Lewis base borane adducts have been measured. Parameterization of these rates has enabled the development of a nucleofugality scale (NFB), shown to quantify and predict the leaving group ability of a range of other Lewis bases. Additivity observed across a number of series R′3-nRnX (X = P, N; R′ = aryl, alkyl) has allowed the formulation of related substituent parameters (nfPB, nfAB), providing a means of calculating NFB values for a range of Lewis bases that extends far beyond those experimentally derived. The utility of the nucleofugality parameter is explored by the correlation of the substituent parameter nfPB with the hydrolyses rates of a series of alkyl and aryl MIDA boronates under neutral conditions. This has allowed the identification of MIDA boronates with heteroatoms proximal to the reacting center, showing unusual kinetic lability or stability to hydrolysis.

Highly efficient one-pot multi-directional selective hydrogenation and N-alkylation catalyzed by Ru/LDH under mild conditions

Atomic economy, non-toxicity, harmlessness and multidirectional selectivity advocated by green chemistry have increasingly become a hot and difficult research topic. Herein, we present a highly efficient, one-pot tandem and easy-to-operate method through which we could directly produce a broad range of multi-directional selective hydrogenated amines or N-alkyl aliphatic amines using aromatic nitro compounds as raw materials. Ru/LDH with characteristics of layered mesoporous structure, well dispersed small Ru nanoparticles and LDH stabilization to the Ru NPs was employed as the catalyst. It is remarkable that multi-directional superb chemoselectivity to aromatic amines, alicyclic amines as well as N-alkyl aliphatic amines could be achieved with excellent catalytic activity and recyclability by tuning reaction conditions over 5wt%Ru/LDH-2. Additionally, this catalytic system also exhibited attractive activity and multi-directional chemoselectivity in the hydrogenation of quinoline and its derivatives with solvents of different polarity. Chemoselectivity to 5,6,7,8-tetrahydroquinoline derivatives could reach as high as 95.6 %.

Understanding the Role of Protic Ionic Liquids (PILs) in Reactive Systems: Rational Selection of PILs for the Design of Green Synthesis Strategies for Allylic Amines and β-Amino Esters

The reactive behaviour of protic ionic liquids (PILs) has been shown to be governed not only by their chemical structures but also by their global compositions, which include the presence of free acids and bases at equilibrium with ionic pairs. Six PILs composed of primary, secondary, or tertiary alkyl ammonium cations with two couterions, nitrate or acetate, were tested in model reactions with unsaturated substrates. The free species that were naturally present in these liquids were identified by cyclic voltammetry. Only tributylammonium nitrate was found to be mostly composed just of the ionic pair; the other five PILs also contain variable amounts of free acid and amine. In reactive systems, these free species determine the products of the reaction. In particular, allylic amines and β-amino esters were obtained in good yields (91 and 75 %, respectively) by reaction of conjugated dienes and acrylates in the presence of PILs. By taking into account the actual composition of each PIL, it was possible to direct the reaction path towards a specific product with good yields, to ensure acid catalysis, to avoid polymerization of the substrate, and to promote phase transfer of products. These results establish some useful guidelines for the rational design of new PIL-based one-step synthetic strategies.

Cobalt-Nanoparticles Catalyzed Efficient and Selective Hydrogenation of Aromatic Hydrocarbons

The development of inexpensive and practical catalysts for arene hydrogenations is key for future valorizations of this general feedstock. Here, we report the development of cobalt nanoparticles supported on silica as selective and general catalysts for such reactions. The specific nanoparticles were prepared by assembling cobalt-pyromellitic acid-piperazine coordination polymer on commercial silica and subsequent pyrolysis. Applying the optimal nanocatalyst, industrial bulk, substituted, and functionalized arenes as well as polycyclic aromatic hydrocarbons are selectively hydrogenated to obtain cyclohexane-based compounds under industrially viable and scalable conditions. The applicability of this hydrogenation methodology is presented for the storage of H2 in liquid organic hydrogen carriers.

Photometric Characterization of the Reductive Amination Scope of the Imine Reductases from Streptomyces tsukubaensis and Streptomyces ipomoeae

Imine reductases (IREDs) have emerged as promising enzymes for the asymmetric synthesis of secondary and tertiary amines starting from carbonyl substrates. Screening the substrate specificity of the reductive amination reaction is usually performed by time-consuming GC analytics. We found two highly active IREDs in our enzyme collection, IR-20 from Streptomyces tsukubaensis and IR-Sip from Streptomyces ipomoeae, that allowed a comprehensive substrate screening with a photometric NADPH assay. We screened 39 carbonyl substrates combined with 17 amines as nucleophiles. Activity data from 663 combinations provided a clear picture about substrate specificity and capabilities in the reductive amination of these enzymes. Besides aliphatic aldehydes, the IREDs accepted various cyclic (C4–C8) and acyclic ketones, preferentially with methylamine. IR-Sip also accepted a range of primary and secondary amines as nucleophiles. In biocatalytic reactions, IR-Sip converted (R)-3-methylcyclohexanone with dimethylamine or pyrrolidine with high diastereoselectivity (>94–96 % de). The nucleophile acceptor spectrum depended on the carbonyl substrate employed. The conversion of well-accepted substrates could also be detected if crude lysates were employed as the enzyme source.

Hexakis [60]Fullerene Adduct-Mediated Covalent Assembly of Ruthenium Nanoparticles and Their Catalytic Properties

The C66(COOH)12 hexa-adduct has been successfully used as a building block to construct carboxylate bridged 3D networks with very homogeneous sub-1.8 nm ruthenium nanoparticles. The obtained nanostructures are active in nitrobenzene selective hydrogenation.

N-ethyl method for preparing cyclohexylamine

The invention disclose a preparation method of N-ethyl cyclohexylamine, which comprises the following steps that an ethylamine aqueous solution is added into a high-pressure reaction kettle; then methanol, ethanol, isopropanol or tetrahydrofuran is added as a reaction solvent; a catalyst, namely palladium or carboplatin, is added; nitrogen is supplied to replace air in the high-pressure reaction kettle; hydrogen is supplied to maintain pressure at 0.5-5Mpa; the temperature is raised to 30-50 DEG C, wherein stirring is performed all the time in the above process; cyclohexanone is driven into the high-pressure reaction kettle by a metering pump, and then heated to 30-150 DEG C, and reacts for 1-10h at the reaction pressure of 0.5-5 Mpa; hydrogen is supplied continuously and the stirring is performed all the time in the reaction process; after the reaction, the temperature in the high-pressure reaction kettle falls to a room temperature, and the pressure is released to normal pressure; discharge is performed; the catalyst is filtered; a filtrate is rectified; and finished N-ethyl cyclohexylamine is obtained. The preparation method has the advantages of simple technology, low cost, high yield, green and environmental protection.

Post-functionalized iridium-Zr-MOF as a promising recyclable catalyst for the hydrogenation of aromatics

The multifunctional heterogeneous catalyst iridium-Zr-based MOF is able to effectively catalyze the hydrogenation of aromatic compounds in high yields under mild conditions. The catalyst was found to be highly active and reusable, giving similar reactivity and selectivity after at least five catalytic uses. This journal is the Partner Organisations 2014.

One pot catalytic NO2 reduction, ring hydrogenation, and N-alkylation from nitroarenes to generate alicyclic amines using Ru/C-NaNO 2

A report to produce alicyclic amines and subsequent N-alkylation with alcohols using Ru/C-NaNO2 catalyzed facile transformation of nitrobenzene was investigated. Effects of solvent, temperature, pressure, reaction time, and molar-ratio of substrate/catalyst on product composition were also studied. These mechanistic studies explain that nitrobenzene undergoes hydrogenation reaction in the following order; -NO2 reduction to -NH2, aromatic ring-hydrogenation to alicyclic, and from the reaction of alcohol to give N-alkylated amines. This investigation shed lights on possible application to polyurethane chemistry since these amines are used as important precursors for diisocyanates.

PROCESS FOR PREPARING SECONDARY AMINES IN THE LIQUID PHASE

The present application relates to a process for preparing secondary amines by aminating excess primary or secondary alcohols with primary amines in the liquid phase in the presence of copper-comprising catalysts.